Combinatorial chemistry is a powerful and well-established means of generating large collections of organic molecules for drug discovery research. 1 With the dawn of the genomics and proteomics era, many of the drug discovery candidates in the future look to be protein, peptide, and perhaps, peptidomimetic based. While extremely potent as therapeutics, protein and peptide drugs are plagued with many stability issues inherent in their complex structures but most notably are their limitations with regards to oral absorption. In research efforts, we have shown that the covalent attachment of proprietary amphiphilic oligomers to protein, peptide, and even small molecule therapeutics alters the physicochemical properties of the drug molecule to overcome those challenges associated with delivery. This conjugation technology has been successfully employed to enable the oral delivery of insulin2a-e and calcitonin2f in addition to demonstrating penetration of the blood brain barrier by enkephalin. 2g Delayed onset of action, stability to enzymatic degradation, enhanced bioactivity, and/or extended duration of action have also been observed through these modifications. To further expedite our drug-conjugate discovery process, it became necessary to possess a compound library containing a wide variety of structurally diverse amphiphilic block co-polymer oligomers. More specifically, the structural differences needed to include permutations around the number of poly(ethylene glycol) (PEG) monomers, the type and length of alkyl chain, and the lability of the drug-oligomer bond, i.e. stable or sensitive to hydrolysis or first pass effects. PEG oligomer libraries were thus designed, each bearing a hydrophilic component, a lipophilic component and a drug-attaching site. As required for our drug discovery research efforts, each library compound should have a weight of 2-5 g and a minimum purity of 90%. Usually, the scale of combinatorial library compounds is only milligrams to tens of milligrams. Construction of this type of larger-scale combinatorial libraries has been difficult and rare.